🍇 About grape:
Our entrepreneurial spirit drives us in what we do and what we are passionate about. Our mission is to become the premier health partner in the insurance business. Recognising the need for innovation in the traditional employee insurance model we are set to revolutionize the employee insurance industry. We help companies support people before and after they get sick and to make more of their time. Our insurance solutions reduce monotonous and manual work for employees, doctors, HR & payroll managers. As we strive to lead a technology-driven transformation, we put employees first.
At grape we pride ourselves on our people and our culture. We continue to grow fast and that’s where you come in. Our team is dynamic, diverse and full of creative ideas. Want to join? We can’t wait to get to know you!
🚀 Your role
We’re looking for a foundational Senior DevOps Engineer to design, build, and own the infrastructure and operational foundations of grape as we scale. This is a highly autonomous individual contributor role: you’ll be the first DevOps engineer, responsible for independently identifying, prioritising, and executing DevOps initiatives across security, infrastructure, CI/CD, observability, and developer experience.
As grape expands its platform, introduces new product systems and scales, the complexity of our infrastructure will grow significantly. Your mission is to make that complexity manageable, secure, and cost-effective—while enabling engineers to move faster and with more confidence.
We operate in a highly regulated insurance and health context, where reliability, security, and trust are non-negotiable. You will establish strong foundations: secure access controls, security-aware engineering practices, optimized CI/CD pipelines, and robust observability across environments.
You’ll work closely with engineering, product, and other parts of the business to define an infrastructure roadmap, improve developer experience, reduce operational risk, and ensure our systems are reliable, observable, and scalable for the long term.
🔍 What you’ll do
Infrastructure & Platform OwnershipTake end-to-end ownership of grape’s cloud infrastructure across environments (development, staging, production).Design and execute an infrastructure roadmap aligned with product growth, architectural changes, and regulatory requirements.Support the evolution from a more monolithic platform toward a more modular and service-oriented architecture.Plan and execute database upgrades and infrastructure changes with minimal risk and downtime.Ensure infrastructure is reliable, scalable, and maintainable as system complexity increases.
Security & ReliabilityEstablish and enforce security-first engineering practices across infrastructure and CI/CD.Improve access control, secrets management, and protection of production systems in line with written policies and best practices.Introduce and maintain dependency audits, security scans, and automated checks in the development lifecycle.Partner with engineers to identify and mitigate infrastructure-level risks early.Help ensure compliance with data protection and security expectations relevant to insurance and health data.
CI/CD & Developer ExperienceOwn and significantly improve CI/CD pipelines, balancing speed, reliability, and cost efficiency.Identify and eliminate unnecessary CI work (e.g. pipelines running for irrelevant changes).Enable engineers to run tests, checks, and validations on demand without prohibitive costs.Improve feedback loops so engineers can ship confidently and frequently.Actively advocate for a great developer experience, reducing friction in day-to-day development.
Observability & OperationsImprove monitoring, logging, and alerting across systems.Define meaningful service-level indicators and alerts that reflect real user and business impact.Ensure issues in production can be detected, understood, and resolved quickly.Support incident response and post-incident reviews, driving continuous operational improvement.
Collaboration & EnablementWork closely with engineers during design and implementation to ensure infrastructure concerns are addressed early.Partner with product and leadership on trade-offs between speed, cost, reliability, and security.Document infrastructure, processes, and best practices to make knowledge accessible across the team.Act as a trusted advisor on DevOps, infrastructure, and operational topics.
💡 What you’ll need
5+ years of experience as a DevOps / Platform / Infrastructure Engineer in a SaaS or cloud-native environment.Proven ability to work autonomously and take ownership as the first DevOps hire or in similarly unstructured environments.Hands-on experience with CI/CD systems (Github actions) and pipeline optimisation.Solid knowledge of cloud infrastructure (GCP) and infrastructure-as-code (Terraform + Terragrunt).Kubernetes/GKE knowledgeExperience improving security posture through access controls, automated checks, and secure engineering practices.Strong understanding of Datadog and other observability tools and practicesExperience planning and executing infrastructure or database upgrades safely.Excellent communication skills and the ability to explain complex infrastructure topics to non-experts.A strong sense of responsibility for reliability, security, and cost awareness.Nice to have:
Experience in fintech, insurtech, healthtech, or other highly regulated environments.Familiarity with compliance frameworks such as GDPR, ISO 27001, or SOC 2.Exposure to cost optimization strategies in cloud and CI/CD environments.Familiarity with monorepo tooling (pnpm, Turborepo)
💬 You’re an ideal candidate for this role if
You enjoy building foundations and structure.You’re motivated by reliability, security, and long-term sustainability—not just quick fixes.You think in systems and trade-offs, balancing developer experience, cost, and risk.You care deeply about protecting sensitive health and financial data.You want to have a high-impact role in shaping how a growing engineering organization operates.
